1-(3-(2-aminoethyl)-5-(3-(trifluoromethyl)-1H-pyrazolo[3,4-b]pyridin-4-yl)phenyl)cyclopropanecarbonitrile

ID: ALA3310283

PubChem CID: 57969582

Max Phase: Preclinical

Molecular Formula: C19H16F3N5

Molecular Weight: 371.37

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  N#CC1(c2cc(CCN)cc(-c3ccnc4[nH]nc(C(F)(F)F)c34)c2)CC1

Standard InChI:  InChI=1S/C19H16F3N5/c20-19(21,22)16-15-14(2-6-25-17(15)27-26-16)12-7-11(1-5-23)8-13(9-12)18(10-24)3-4-18/h2,6-9H,1,3-5,23H2,(H,25,26,27)

Standard InChI Key:  NWVGJYALUCYJKL-UHFFFAOYSA-N

Molfile:  

     RDKit          2D

 27 30  0  0  0  0  0  0  0  0999 V2000
   20.8993  -12.1481    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.4930  -12.8571    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   21.3102  -12.8545    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.7733   -8.4773    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.7722   -9.2968    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.4802   -9.7058    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.4785   -8.0684    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   19.4819  -10.5208    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.7725  -10.9286    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.7719  -11.7451    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.4801  -12.1546    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.1902  -11.7418    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.1873  -10.9268    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.0639  -12.1531    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.3565  -11.7440    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   21.6057  -11.7372    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   22.3105  -11.3227    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   20.1871   -8.4737    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.1873   -9.2969    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.9703   -9.5510    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   21.4540   -8.8849    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   20.9699   -8.2191    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   21.2230  -10.3282    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.6764  -10.9356    0.0000 F   0  0  0  0  0  0  0  0  0  0  0  0
   22.0224  -10.4979    0.0000 F   0  0  0  0  0  0  0  0  0  0  0  0
   21.4327  -11.1146    0.0000 F   0  0  0  0  0  0  0  0  0  0  0  0
   17.3571  -10.9268    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
  2  1  1  0
  3  2  1  0
  1  3  1  0
  4  5  2  0
  5  6  1  0
  6 19  2  0
 18  7  2  0
  7  4  1  0
  8  9  2  0
  9 10  1  0
 10 11  2  0
 11 12  1  0
 12 13  2  0
 13  8  1  0
  6  8  1  0
 10 14  1  0
 14 15  1  0
 12  1  1  0
  1 16  1  0
 16 17  3  0
 18 19  1  0
 19 20  1  0
 20 21  2  0
 21 22  1  0
 22 18  1  0
 20 23  1  0
 23 24  1  0
 23 25  1  0
 23 26  1  0
 15 27  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA3310283

   1-[3-(2-aminoethyl)-5-[3-(trifluoromethyl)-2H-pyrazolo[3,4-b]pyridin-4-yl]phenyl]cyclopropane-1-carbonitrile

Molecule Features

Natural Product: No

Oral: No

Chemical Probe: No

Parenteral: No

Molecule Type: Small molecule

Topical: No

First In Class: No

Black Box: No

Chirality: No

Availability: No

Prodrug: No

Calculated Properties

Molecular Weight: 371.37

Molecular Weight (Monoisotopic): 371.1358

AlogP: 3.70

#Rotatable Bonds: 4

Polar Surface Area: 91.38

Molecular Species: BASE

HBA: 4

HBD: 2

#RO5 Violations: ┄

HBA (Lipinski): 5

HBD (Lipinski): 3

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 9.42

CX Basic pKa: 10.03

CX LogP: 2.44

CX LogD: 0.83

Aromatic Rings: 3

Heavy Atoms: 27

QED Weighted: 0.73

Np Likeness Score: -0.48

References

1. Clemens JJ, Coon T, Busch BB, Asgian JL, Hudson S, Termin A, Flores TB, Tran D, Chiang P, Sperry S, Gross R, Abt J, Heim R, Lechner S, Twin H, Studley J, Brenchley G, Collier PN, Pierard F, Miller A, Mak C, Dvornikovs V, Jimenez JM, Stamos D..  (2014)  Strategies for the modulation of phase II metabolism in a series of PKCε inhibitors.,  24  (15): [PMID:24939756] [10.1016/j.bmcl.2014.05.082]

Source

Source(1):

• Scientific Literature